A Successful Late-Night DM

This is my first attempt at writing a story. Feedbacks are welcome.

This started back when we were still in high school. I was already graduating, 18 years old, while Steph was 16, still in her junior year. Our ages didn’t line up, so I really didn’t do anything back then. I just stayed quiet and simply thought she was beautiful.

Fast forward four years later. Throughout all that time, we still didn’t know each other. Until one day, I came across her VSCO. It’s like Instagram, but with more raw pictures, no captions, no effort, no extra flair. Usually thats where photos end up that cant be uploaded to IG. Thats where I saw a side of her I didnt know existed. She had a wild side. Of course, I just quietly stalked. She was already beautiful before, but from what I saw there, she was even more so. Thats when I immediately thought of a smooth but flirty icebreaker.

After a day, she replied. We talked about how I found her, why I DM’d her. The usual questions. I also found out she had just come out of a breakup. For me, it was perfect timing. I just kept talking to her. Some flattery here, some affection there. Until eventually, she gave in.

She also said that we could go out, but only as friends for now. She said she wanted a break from relationships and dating. That was fine with me. I didn’t really plan on taking it seriously anyway. I just found her very attractive.

I agreed to the “friendly date.” Her plan was: a movie, then a late night drive. Of course, I was game. She chose the movie one from the After series because that was the only option. When we went inside, it was almost all couples. She sat in the middle, probably to be safe. But she did agree to let me put my arm around her while we watched.

I wasnt really focused on the movie anymore. I was already thinking about where we could drive afterward. When the movie ended, we went straight to the car. We had been driving around and talking for about 45 minutes when her mom called and told her she needed to come home. It was already 11:30 at night. We were still a bit far, so it was another 30 minute drive back to her place.

When we arrived in her neighborhood, I asked if we could park on the side for a bit. She agreed. We just chilled until she really had to go home.

We hugged before saying goodbye. When we pulled apart, I suddenly said, “I wanted to kiss you.” That did it. We started making out, exchanging saliva. Probably a solid minute straight. One of my hands was on her breast, squeezing it, and the other was on her lower back, feeling her soft skin.

She took off her shoes and climbed onto me in the driver’s seat. We were still kissing, her chin and neck soaked with my saliva. Our kissing was extremely sloppy. I started taking off the long-sleeve top she was wearing, and that’s when her beautiful body and breasts were revealed. Probably a 32C. I’m not sure. Her areolas and nipples were brown and slightly pinkish. I immediately sucked and licked them, then lowered the seat and licked her cleavage down to her navel. I looked at Steph first to see if it was okay to unzip her jeans. She just nodded, so I opened them and pulled them down, revealing the black lace panties she was wearing. I kissed and licked them right away. I just moved the panties to the side so I could lick her directly. Very clean, shaved, and smelled good. Her juices tasted like water. Very good hygiene. She was already soaking wet—from her juices and my saliva. She was just sitting on my face, moaning in pleasure.

After a few moments, I asked her if she wanted me to put it in. She hesitated, then refused and said we should save it for the bedroom. She sat back down in the passenger seat and put her pants back on.

I kissed her again and said, at least make me cum. So I took her hand and guided it to my very hard cock. “I need head,” I said. She replied, “I’m not very good at it.” “Just try and make me cum.” She did. She wasn’t very good, but she knew what she was doing. I was getting close. I told her I was going to have to cum in her mouth and that she should spit it out afterward because I didn’t have any tissues. I came inside her mouth. She tried to swallow but almost gagged, so she spit everything out onto my cock.

I kissed and licked her breasts again before she got down. I drove her right up to the front of her house, and that’s where we finally parted ways.